7 Jeans Outfits for Women Over 50 That Feel Comfortable All Day

Jeans outfits for women over 50 - cropped wide-leg jeans with a blue floral shirt, brown loafers and a brown leather bag on an autumn sidewalk

* This post contains affiliate links. If you buy through them I may earn a small commission, at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

I still wear jeans all the time. I just don't wear them the same way I did 15 years ago.

For one thing, my body is different. I want a little more room in some places, a little more structure in others, and I have absolutely no interest in spending the day pulling up a waistband or wondering why the pockets are sitting halfway down my thighs.

But the bigger change has been how I style them.

A good pair of jeans can still be one of the hardest-working things in your wardrobe after 50. The best jeans outfits for women over 50 start with finding the shapes that suit you now, then knowing what to wear with them.

So I put together seven fall outfits using five jean styles and pieces that are easy to wear in real life. These jeans outfits for women over 50 are meant for ordinary days, not for photographs.

Nothing terribly complicated. No jeans that require an explanation before you put them on.

And please don't think you need to buy five pairs of jeans. Look at what you already have first. If you own something similar, use it.

If you would rather start from complete outfits than from the denim itself, I put together ten comfy fall outfits a few weeks ago.

The 5 Jeans I'm Using

Straight-Leg Jeans

If I could only keep one pair, I would probably keep a straight leg.

They work with loafers, boots, flats, blazers, sweaters and jackets, and they don't date as quickly as some of the more dramatic denim shapes.

Straight-leg jeans for women over 50 in a medium blue wash Shop Now

Wide-Leg Jeans

I like a wide leg when I want something a little more relaxed.

The important thing with wide leg jeans for women over 50 is the fit around the waist and hips. I want the jeans to fall nicely from there, not add a great lump of fabric where I don't need one.

Wide leg jeans for women over 50 in a faded blue wash Shop Now

Cropped Wide-Leg Jeans

These are especially good with flats and slingbacks because you can actually see the shoe.

They're also worth trying if you've put on full-length wide-leg jeans and immediately thought, Absolutely not.

Sometimes it's the length that's bothering you, not the wide leg itself.

Cropped wide-leg jeans with patch pockets in a light blue wash Shop Now

Dark Straight-Leg Jeans

Dark denim is my answer when I want to wear jeans but need to look a little more pulled together.

They're still comfortable and casual, but they don't have quite the same weekend feel as faded blue denim. Dark jeans over 50 are the easiest way I know to make denim look deliberate rather than accidental.

Dark straight-leg jeans in a deep indigo wash with no fading Shop Now

White Straight-Leg Jeans

I'm keeping my white jeans out for fall.

There is no reason to pack them away simply because summer is over. They just need different clothes around them.

White straight-leg jeans in a substantial off-white denim Shop Now

Three Bags I'll Use More Than Once

You'll notice the same bags appearing throughout these outfits.

That's deliberate.

Most of us are not changing handbags every morning to coordinate with a Pinterest board. I would rather own a few good bags that work with lots of clothes. All seven jeans outfits for women over 50 below use one of these three.

Burgundy leather shoulder bag with a tassel charm

Burgundy Purse

Shop Now
Soft brown suede tote bag with slim shoulder straps

Brown Suede Tote

Shop Now
Black pebbled leather bucket bag with a gold clasp

Black Leather Purse

Shop Now

Seven Jeans Outfits for Women Over 50

Now, let's get dressed.

1. Chocolate Brown, Stripes and Jeans

Brown cropped jacket + striped sweater + wide-leg jeans + brown flats + brown suede tote

Jeans outfits for women over 50 - brown cropped jacket, navy striped sweater and wide-leg jeans with a brown suede tote

Shop this look

Shop Now

I've been wearing much more brown lately.

If you usually reach for black whenever an outfit needs a darker color, chocolate brown is worth trying. It looks lovely with denim, particularly the lighter and medium washes, and feels a little softer around the face.

For this outfit, I paired a cropped brown jacket with a striped knit and wide-leg jeans.

The shorter jacket matters. Because there is already plenty of fabric in the jeans, I don't want a long, heavy jacket covering everything on top as well.

Then I kept the shoes and bag brown.

You could certainly add a black bag instead, but I wouldn't. We've got a perfectly nice thing going here. No need to invite black along just because it normally comes to everything.

I also added a bag charm for a little personality.

What I'd pay attention to: If you carry more weight around your middle, the jacket doesn't need to be very cropped. Look for one that finishes around the top of the hip rather than directly at the waist.

2. White Jeans in Fall

White straight-leg jeans + crewneck sweater + barn jacket + black ankle boots + black purse

White straight-leg jeans for fall with a cream barn jacket, black sweater and black ankle boots

Shop this look

Shop Now

Every September, white jeans apparently receive an eviction notice.

I ignore it.

White denim works perfectly well in fall. I simply stop wearing it with obviously summery pieces.

Here I've added a crewneck sweater, barn jacket and black ankle boots. Now there is nothing particularly summery about the outfit.

I like the black boots and bag because they give the white jeans a bit of contrast. The jacket brings some warmth back in so the whole outfit doesn't become black-and-white and severe.

And this is something I wish more women did before getting rid of clothes.

If something suddenly feels wrong, try changing the pieces around it first.

Your white jeans may be perfectly innocent.

What I'd pay attention to: With white denim, fabric matters. I prefer a substantial denim that doesn't show every seam, pocket lining and detail underneath.

3. Denim With Suede and Burgundy

Brown suede bomber + denim shirt + straight-leg jeans + burgundy loafers + burgundy bag

Brown suede bomber jacket with a denim shirt, straight-leg jeans and burgundy loafers

Shop this look

Shop Now

A denim shirt with jeans can go one of two ways.

Done well, it looks relaxed and modern.

Done badly, you may feel you've accidentally dressed for a country music video.

The suede jacket helps enormously here.

It breaks up the denim and gives the outfit some texture. Then I've added burgundy loafers and a burgundy bag.

I love burgundy with blue denim. It gives you color without being loud, and using it twice makes the outfit look as though you thought about it - even if you were dressed and downstairs in eight minutes.

The jeans are straight rather than very wide because the bomber already has some volume.

I added a brown belt and gold earrings as finishing touches.

What I'd pay attention to: Your denim shirt and jeans don't have to match. In fact, I usually prefer a little difference between the washes.

4. Jeans and a Blazer Without Looking Like You're Going to Work

Straight-leg jeans + turtleneck + blazer + suede loafers + suede tote

Jeans outfits for women over 50 - checked blazer, cream turtleneck and straight-leg jeans with brown suede loafers

Shop this look

Shop Now

If you worked in an office for years, you may have developed a complicated relationship with blazers.

Put one on and suddenly you feel you should be carrying a laptop and asking when everyone is free for a meeting.

But I still love them.

The difference is what I wear with them now.

Here I've used straight-leg jeans, a simple turtleneck, brown suede loafers and a suede tote. The jeans and suede take away the business feeling, while the blazer gives the outfit enough structure to look polished.

This is exactly the sort of outfit I like for lunch, shopping, traveling or any occasion where I want to look nice without actually being dressed up.

And that's a category of clothing I need much more than cocktail attire.

What I'd pay attention to: If your middle has changed, try wearing the blazer open. You still get the structure at the shoulders without fastening it across the waist.

5. Double Denim

Denim shirt + wide-leg jeans + striped sweater + brown suede boots + brown tote

Double denim outfit with a denim shirt, wide-leg jeans and a brown striped sweater over the shoulders

Shop this look

Shop Now

Yes, I'm doing denim with denim again.

This time with a wide-leg jean.

I don't spend any time trying to find two denim washes that match exactly. I'd actually rather they didn't. Once everything is the same shade of blue, it can start looking like a uniform.

The striped sweater adds another layer, and all the brown - boots, belt and suede bag - warms up the blue.

This is also a good example of why accessories matter more than we sometimes think. Most jeans outfits for women over 50 are made or undone by what you add at the end.

Take away the belt, bag and boots and you have a denim shirt and jeans.

Add them back and you have an outfit.

I know which version I'd rather leave the house in.

What I'd pay attention to: If a full denim shirt feels bulky tucked into your jeans, don't force it. Try a partial tuck, leave it untucked if the length works, or wear it open over a thinner top.

6. Cropped Jeans and a Floral Shirt

Cropped wide-leg jeans + floral shirt + long cardigan + burgundy bag + slingback flats

Cropped wide-leg jeans with a floral shirt, long navy cardigan and burgundy slingback flats

Shop this look

Shop Now

This outfit feels a little softer than the others.

I started with a floral shirt, added cropped wide-leg jeans and then brought in the longer cardigan.

What I like here is the contrast in proportions. The cardigan gives you that lovely long line, while the jeans stop above the shoe instead of continuing all the way to the floor.

And if I've chosen a pretty slingback, I would quite like it to make an appearance.

I added the burgundy bag because there is already enough going on in the shirt. I don't need another print or another statement accessory competing with it.

One print is doing the job. I let it.

What I'd pay attention to: Cropped jeans can be awkward when they finish at the widest part of your calf. An inch or two can make a surprising difference, so pay attention to the hem rather than assuming cropped jeans simply don't suit you.

7. Dark Jeans When You Want to Look a Little Thinner

Dark straight-leg jeans + printed cardigan + black top + black ankle boots + black purse

Dark straight-leg jeans with a printed green cardigan, black top and black ankle boots

Shop this look

Shop Now

There are days when regular blue jeans feel a little too casual but dress pants feel like more effort than I'm prepared to make.

That's when I wear dark jeans.

For this outfit I've kept the base very simple: dark straight-leg jeans, a black top, black ankle boots and a black bag.

Then the printed cardigan goes over everything.

Because the jeans are dark, they blend more easily with the black pieces and create a cleaner line through the outfit.

I particularly like this combination for dinner, traveling or those invitations where somebody has written “smart casual” and left the rest of us to work out what on earth they mean.

What I'd pay attention to: Look for dark denim without lots of fading or whiskering if you want the smartest version. The cleaner the wash, the easier it is to dress up.

Begin with the free guide.

The answer isn’t a bigger size.
Learn to read what’s actually wrong with a garment, and what to look for instead.

No spam. Unsubscribe anytime.

How to Wear Jeans Over 50 When Your Body Has Changed

If jeans have become harder to buy, you're not imagining it.

A pair that looked wonderful on you years ago may not be the pair you'd choose today. Your waist may sit differently. Your tummy may be softer. Your hips may have changed. You may want more room through the thigh. Or you may simply be finished with wearing clothes that are uncomfortable for the sake of looking slimmer.

Good.

At this point, I think we've earned the right to sit through lunch without secretly unbuttoning our jeans under the table.

Try different rises. Try the next size. Try straight instead of skinny. Try wide instead of straight. Have the hem altered if everything else fits beautifully.

And don't become too attached to the number on the label. Nobody can see it once your jeans are on.

What people can see is whether your clothes fit you well and whether you look comfortable in them.

That's what I'm interested in. And that is what I was really after with these jeans outfits for women over 50: clothes that look considered and feel like nothing at all.

If you've reached the point where your body has changed and you're standing in front of a closet full of clothes thinking, “I have plenty to wear, so why does nothing feel right anymore?”, I made my free guide for you.

Get the free guide - Your Body Changed. Now What Do You Wear?

It will help you start dressing the body you have today, instead of constantly trying to make your old wardrobe work on a body that isn't quite the same anymore.

0 comments

No comments yet. Tell me what you think, sweetheart.

Leave a comment

Comments appear once I have read them.

← More on the blog